Rearrangement of methylenecamphor during electrophilic bromination: remarkably clean access to the unnatural fenchyl (1,3,3-trimethylbicyclo[2.2.1]heptane) system

Authors
Thomas, AA Monk, KA Abraham, S Lee, S Garner, CM
Citation
Aa. Thomas et al., Rearrangement of methylenecamphor during electrophilic bromination: remarkably clean access to the unnatural fenchyl (1,3,3-trimethylbicyclo[2.2.1]heptane) system, TETRAHEDR L, 42(12), 2001, pp. 2261-2263
Citations number
12
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
42
Issue
12
Year of publication
2001
Pages
2261 - 2263
Database
ISI
SICI code
0040-4039(20010318)42:12<2261:ROMDEB>2.0.ZU;2-V
Abstract
Treatment of (+)-methylenecamphor (2) with NBS in the presence of pyridine resulted in a rapid and remarkably clean rearrangement to yield a brominate d (+)-methylenefenchone (3) in high yield and purity (>96%). The structure of the product was established by X-ray crystallography and the stereochemi stry confirmed by both polarimetric and chiral GC analyses. Two transformat ions of the product were also performed to elucidate the structure. (C) 200 1 Elsevier Science Ltd. All rights reserved.